Life in a Skirt
by YaoiloverXD
Summary: All Dean wanted in his life was to make his father proud. Dean knows to do this he needs to get into Supernatural Academy, but there were no room left for boys, so Dean's life long friends come up with a plan in order to get him into the school. What will this new school bring for Dean.
1. New school, New life, New everything

**Hi everyone this is my new story and this time it is for supernatural. It is my first one and I hope that you all like it :)**

 **Chapter 1 New school, new life, new everything**

"Come on I know that you will look good in it. Besides you want to go to school with me Jo and Meg, right?" Charlie said as she tried to get her best friend out of the bathroom.

"Of course I do but I am going to look ridiculous." Yelled Dean from in the bathroom which charlie had convinced him into.

"Please just come out, if you look ridiculous than you don't have to wear it and then we will find somewhere we all can go to school." Charlie said as a compromise to Dean.

"Fine." Dean said knowing that there was no way he was going to get out of the bathroom, and prove his point other wise.

Dean opened the door to the bathroom and stepped out of it. He knew that he looked ridiculous but not so bad that he shocked all of his friends. Dean turned in order to go back into the bathroom so he could just put back on his band t-shirt and jeans but Charlie grabbed his arm.

"Damn, Dean. If I did not know you were a boy I would be hitting on you right now." Charlie said with amazement in her eyes.

"Okay, now you are just making fun of me." Dean said

"No she is not kidding, you look like a hot girl. Maybe it is your bowed legs working to help you, all I know is that you look like a girl and you look good in the school uniform. Now we can all go to the school!" Jo said getting excited.

"Yeah whatever, but I am guaranteeing that everyone will find out soon." Dean said with a smirk on his face.

The whole reason that Dean has to dress up and a girl in the first place is because all the boy places for Supernatural Academy had been filled when Dean had tried to enroll, but Charlie had an idea, that idea was to have Dean dress in one of their school uniforms to see if he would look good in it or not. Dean had a girlish figure because he was to busy studying to workout, like others his age. Now that had come in use. Dean was happy that he got to go to the same school as his older brother. This was what he had been studying for all this time. It made him so happy when he had passed the exam, but there was no space for him because all the boy spots had been filled.

Now here Dean is on the day to move in wearing his own uniform. He had a pixie cut at the moment because he was doing the finale cram and he had not cut his hair in about a month, so his hair had grown longer than his usual short short hair. He was wearing his usual black framed glasses and of course the girls uniform. It was mostly white except for the school emblem on the right breast pocket of the blazer. There was also a blood red sweater vest and then a white dress shirt. The skirt was also white, There were also knee high blood red socks and then the shoes for the girls were black Mary-jeans. The boys had the same uniform except the skirt is replaced with pants that are the same color, and they were dress shoes instead of Mary-jeans.

Dean waited at the gate for a few minutes he finally caught the sight of Charlie, Jo, and Meg coming his way.

Dean ran over to meet them.

"Hey guys, what took you so long." Dean said with a smirk their way.

"We were just trying to find matching panties, DD." Meg said with a smirk.

"Why are you calling me that, and really?" Dean asked with a slight blush on his face.

"No she is just messing with you. She is calling you that because we like it more then Deanna." Jo said with a smile.

"Oh okay." Dean said.

"So... Sister from another mister, are you wearing panties or briefs." Charlie said with a smirk.

"P-Panties." Dean said with a blush.

"Really, can I see, I just want to make sure that you are telling the truth." Charlie said with a smirk.

"No you can not. We are outside might I remind you." Dean said with a blush.

"It okay, Charlie I can fix this problem." Meg said with a smirk. Before Dean could even protest she lifted up his skirt.

"Oh pink stain, nice choice." Meg said with a smirk.

"Okay you have seen them now put down my skirt enough people have already seen them." Dean said with a blush covering his face.

"No we need to make sure you are wearing a matching bra." Meg said with a smirk on her face.

"Please just stop." Dean said trying to save himself from getting even more embarrassment on the first day on school.

"Meg don't, she does have a matching bra, I know this because I gave he a bunch of my old ones." Jo said trying to make sure she said she and not he.

"Yeah okay just tell the whole school why don't you. Also thinking about earlier why don't you call me Dean from short, I mean I don't like the nickname DD." Dean said with a sour look on his face.

"That is the point of nicknames DD." The short haired blond said with a smirk on her face.

"Whatever you say Meg." Jo said with a bit of sass in her tone.

"Come on guys lets head inside, we are going to miss introductions and where we have to go to for our dorm if we don't go now." Charlie said trying to get them all inside so they would not be in trouble by not being able to find their dorm.

"Okay" The three others said at the same time causing Charlie to laugh.

Heading inside Dean kept getting a bunch of cat-calls. He was bushing from his neck to the top of his head by the time they were finally inside the entertainment hall that the girls were suppose to be in they were laughing about how the guys of the school were reacting to Dean.

"Hey guys, what did you put that my name was?" Dean asked he was curious.

"Oh we put Deanna. You were named after your Grandmother but that was changed to a boy name but we just changed it to be what the original name was. Is that okay with you DD." Charlie asked.

" That is fine. Thank you." Dean said with a smile on his face.

"No problem DD." Charlie said with a smile on her face.

"So I noticed that you just got used to us calling you DD." Meg pointed out with a smirk on her face.

"Yes I have, please just leave it alone. I am trying to pretend like you have called me that all my life." Dean said trying to get them to understand.

"That makes sense." Meg said.

They stopped talking for a little while waiting to hear what the girls dorm leader had to say.

"Okay now that you are all here I would like to say how happy were are that we got more girls here this year then last year. Now I am going to give out your class number. Everyone in here is a first year, because the other class years are going to have their meeting later. Anyway after I give you your class number make your way to your class room. From there you will be given your dorm." The girls dorm master told them all.

It took a little while but all three girls learned that they were in the same class. They were all in is class four out of the eight classrooms that there was.

The group of girls walked into their classroom and saw that most of the seats were filled in by boys. Then again there were a lot of boys in this school or they would not have denied Dean just because he was a boy.

There was a sit were someone could sit next to the other Dean and Charlie ran over to them. They were the shyness of their group and they refused to sit next to more than one stranger to their side.

They made it to the seats before Jo and Meg understood what was happening. They look over where they had gone to and they curse low under their breath. They were both a little angry and understood. Dean and Charlie were both the youngest in the group and the closest to each other. So it only made sense to let them have the two seats next to each other, but that did not mean that both Meg and Jo where not going to put up a fake hissy-fit about this.

Meg and Jo both headed to other chairs that were all the way across the room for the others. It did not bother them much, they were both outgoing enough that they could deal with more than one stranger at a time.

They had to wait a couple minutes to walk into the room, in that little bit of time Dean and Charlie got into a huge debate about who was the best character in _Bleach_. Dean was a huge Ichigo fan, while Charlie loved Nel, both adult Nel and child Nel. It was starting to get to the point of screaming right before the teacher walked into the room.  
When Charlie and Dean heard the door open they stopped their debate with a silent agreement to settle it later.

Looking up at the teacher, Dean saw the last person he expected to see, Bobby.

Bobby is more Dean's father than Dean own father. Dean know right away that he would recognize the name that he was using and just by the way he looked even if he was dressed in woman's clothes. Dean knew that he would not say anything in front of the class, but that did not mean that there was not going to be a huge discussion of him trying to understand what the hell Dean is doing in a skirt. It would not be a bad conversation but it would be hard to put into words why he had to do this.

"Alright, quiet down and let's get down to roll call." Bobby said as he started to call roll. It took a while but he finally got to the last on the names.

"... Deanna Winchester?" Bobby said making a confused face at the name that was on the paper that he was reading.

"Here." Dean said raising his hand, as there was no way out at this point.

Bobby looked shocked for a minute before he went on like nothing happened.

"Charlie Bradbury?" Bobby called out to which she replied with a causal "Hey"

The last name to be called was someone that Dean knew a while ago and refused to have anything to do with him now because of the huge mistake that he made all those years ago.

"Castiel Novak?" Bobby asked one last time.

A voice came from right next to Dean. "I am here." Castiel said with a monotone voice.

 **Hey everyone what do you think of it. I hope that you all like it. I took me three days to make this chapter but it is longer than my normal chapters.**

 **Please tell me what you think**

 **See you next time :)**


	2. All these years

**I hope that you liked the last chapter. I am really sorry for the late update bu I have to finish school and writer's block sucks :( Anyway enjoy the chapter :)**

 **Chapter 2 All these years**

Looking to where the voice was coming from Dean realized to late that he was sitting next to Castiel. This was not good for Dean. He knew that Cas would be able to tell him apart even in these clothes. They were best friends at one time.

Looking at Cas, Dean realized that he had changed over the years just like Dean had. At one time in his life Dean was fit and Cas was a nerd, but it seems like the tables have turned. Cas was handsome. He was a punk now too, the tips of his hair dyed a blue that matched his eyes, he was also covered in tattoos and piercings but not to much for it to be nasty, but just enough to be riding that line. That was something that Dean never would have expected from the sweet little Cas that he had once known. Then again that was years ago. Dean was very different than anyone ever would have thought that he would have turned out to be in high school. Even Dean thought that he was going to be a manly-man, a jock, the embodiment of what most thought that a high school boy should be, yet here he was cross-dressing in order to stay in this school, and sadly or not so much he was pulling it off well.

For what felt like a long time Dean wondered if Cas was going to recognize him. He waited for the gasp of surprise or even recognition on his face or in his eyes, but Cas seemed not to notice, or even to remember him. This thought depressed Dean but he knew that he could not show that on the outside.  
'That right Dean this is good he does not know that this is you, this means that you get to stay in this school and don't have to worry about disappointing dad or Sammy. You have to suck it up.' Dean thought to himself. He had to to this for his dad and Sammy.

Looking over at Charlie he could tell that they were going to have a talk later.

'Damn it, I should have known that I could not hind anything from Charlie. I bet she can tell that that is Cas and she can just see the depressed waves coming from me. Damn she is to good." Dean thought with a slightly depressed that he was going to have to be even more girly then he already was.

'oh well I better listen to bobby.' Dean thought trying to pay attention to what Bobby was saying.

Cas' pov

I knew that I was going to hate it here. There was a fucking dress code. I already got stares from almost everybody in this fucking school because I dared to be different. I had to put on the whole uniform. I tried to get away with just the shirt, pants, and shoes, but they made me put it on in the office as soon as one of the teachers saw me in just part of my uniform. It was a pain in the ass, I am only in this school for two reasons one that I might see my old childhood friend Dean, and the other was because my father runs this school so I have to go here just like all of my other brothers and sisters. It sucked but I knew that there was no other way.

Sitting in my seat I waited for my teacher to get in the room. I got here about ten minutes ago and I sat all the way in the back so that there was less on a chance that I was going to have to sit next to someone. But it seems that luck was not on my side because I see four girls at the doorway as they look for seats to sit in, most likely trying to find a set of seats that they all can sit in next to each other, but I seems that the room is more packed then I had thought that it was, there were exactly four seats left and two of them were by me.

I see the bright red head and one of the three blonds run for the seats by me while the other two quietly and in no rush sit in the other two sits that were no where near each other and they seemed just fine with that while the other two were happy that they got to their seats not long after they started to argue about Bleach which it is cool that they have watched it, but I wish they would quite down, lucky for me it was not long before they did just that.

I saw the teacher walk in a couple minutes later and he told us all to be quite, not that I was talking to me. He started to call all of our names.

First he did not call all of them in order like most teachers and second he had a very deep voice almost like mine. I heard he call a Deanna Winchester with a more questioning voice then normal. I just decided to pretend that I did not notice not like I should care. The blond next to me answered and she seem seemed like she would ratter be anywhere but there in that moment but the teacher just continued on the the red head she just said a simple "hey". Next I was called I answered in a normal "i am here" as soon I said this the blond girl next to me turned her head. She looked at me with both worry and with hope, like I was suppose to know who this strange girl was. Sure she was pretty but I was not going to hit on her, she was going to have all to boys after her.

Now that I think about it I do recognize her she was one of the few students that made it here by scholarship, I remember because father had shown me her picture along with others that made it here by the same means the red head was another.

It took me a little bit of time and the girl kept looking to the front of the room only to turn back to me just to stare for a few minutes before repeating this over and over. When she finally looked back at me I had shown that I had recognized her with just my eyes she had worry, hope, and depression in hers. Like she did not want me to see her. I don't understand why but whatever not like someone that pretty was going to talk to me anyways.

I turn around to the front of the room to pay attention to the rest of the what the teacher had to say.

 **Okay everyone I hope that you like this chapter it took me forever to get an idea but I decided to go with cas' pov that helped a lot.**

 **I hope you all enjoyed :)**

 **See you next time**


	3. AN

**I am sorry about not updating this story I am workking on it I promise and I am not going to abandon it. Sorry about the delay but I have a lot of problems with my health. I am slowly working to get this chapter finished. I figured I should put this AN here for all of you just so you know that this story is being worked on just at a very slow pace.**

 **~YaoiloverXD**


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